


dare, obviously

by jhoom



Category: Supernatural
Genre: First Kiss, Fluff, Friends to Lovers, M/M, Sam Is A Sneaky Bastard, Truth or Dare, high school!au
Language: English
Status: Completed
Published: 2016-09-14
Updated: 2016-09-14
Packaged: 2018-08-15 00:53:24
Rating: General Audiences
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 939
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/8035942
Author URL: https://archiveofourown.org/users/jhoom/pseuds/jhoom
Summary: The gang decides to play truth or dare, and it's all fun and games until it's Castiel's turn.





	dare, obviously

**Author's Note:**

> this is complete fluff i'm not even sorry. based on [this post](http://destieldrabblesdaily.tumblr.com/post/150396887169/dean-getting-dared-to-ask-castiel-out-castiel)
> 
> i'm on tumblr [@jhoomwrites](http://jhoomwrites.tumblr.com)

Thursday evenings were spent in the Winchester basement, their group of friends sprawled over the couches with their homework and textbooks in tow.  Today, however, was different.  Spring Break was about to start that weekend, so there were no tests to study for and no pressing assignments to finish. 

So the books were left forgotten, they made some pop-corn and settled in for a night of chatting and hanging out.  Somewhere along the lines, though, Jo huffed in boredom and demanded they play a game.

“What about truth or dare?” Garth suggested.

“Oh my god yes yes yes yes yes!” Charlie squealed.  “PLEASE!  Oh please oh please!”

“Good job, Garth, I think you broke her.”  Dean rolled his eyes.  “Charlie, truth or dare?”

“Dare.  Obviously.”

“I dare you to kiss a boy,” he countered immediately.

Charlie rolled her eyes.  “That’s not even a hard one.”  She immediately walked over to Garth and planted a big one on his cheek.  He blushed like a tomato but smiled smuggly at Dean. 

“Garth, she’s into chicks.  Don’t let it get to your head.”

“Dean, don’t be mean,” Charlie scolded.  “Truth or dare, Winchester?”

“Dare.  Obviously,” he parroted her words back to her, arms crossed his chest in challenge.

“I dare you to say something nice about everyone in this room.”

“ _What?”_

Castiel couldn’t help but laugh.  They all knew Dean cared about them, but he was practically allergic to verbally expressing those sentiments.  Dean closed his eyes to mentally prepare himself, then said through gritted teeth, “Charlie, you are the coolest person I’ve ever met.  Jo, I love how spunky you are.  Garth, I know I say it’s stupid but I think it’s awesome how friggin nice you are all the time.  Cas, I’m glad you’re my best friend.  Sam, you’re not a complete dweeb.”

Charlie _ahemed_  loudly at the last one, so Dean flicked her off and added in a rush.  “ _Fine_.  Sam, you’re really smart and I’m proud of you.  Better?”

“Much,” she beamed at him.  “And damn right I’m the coolest.”

“I hate you.”  

They kept going around and around, asking silly questions and doing hilarious (but reasonable) dares.  Finally, Sam rounded on Cas.  

“Truth or dare, Cas?”

Castiel’s already gone a few times and chosen truth.  But it’d been Garth and Charlie asking before, and they always threw him soft questions.  He felt suddenly daring, and decided to give himself a challenge.  “Dare, please.”

“Okay, uh…”  Sam was obviously thrown off, but he recovered quickly.  Clapping his hands together and smirking evilly, he said, “I dare you to say yes to any question you’re asked for the next 24 hours.”

They still had school the next day, which meant he was no doubt in for some embarrassing questions from his friends.  But it was part of the game, and he didn’t mind.  If his friends got some amusement from it, then he was okay with it.  He shrugged.  “Alright, fine.”

Their eyes lit up and, since apparently they wanted to verify he’d actually do it, they started hounding him.

“Cas, do you love the pranks your big brother pulls on you?”

“Yes, Garth.  I love when I wake up with my hair dyed blue or find sandpaper glued to the insides of my shoes.”

“Cas, do you think you look ridiculous in that oversized trenchcoat?”

“Yes, Jo.  I clearly don’t enjoy the warmth it provides and only wear it for comedic effect.”

“Cas, hon, am I your bestest friend?”

“Yes, Charlie, of course.”

“WILL YOU GO OUT WITH ME?”

The laughter and giggles immediately stopped as they all turned to stare at Dean.  He was panting like he’d just run a marathon and he was so red you couldn’t see any of his freckles.  

“Uh,” he stammered, heart pounding in his chest.   Was it hot in here?  It felt hot.  “What?”

“Will you… you know… go on a date with me?”

The group wordlessly turned from Dean to Cas back to Dean.  Charlie nudged Castiel’s foot, stage whispering, “Don’t forget your dare.”

“Yes, Dean,” he croaked out.  “I’ll go on a date with you.”

“Good, good.”  Dean stood up and started inching forward.  “You wanna get burgers at the Roadhouse?”

Following Dean’s lead, he stood up as well.  “Yes, Dean.”  

“Then you wanna go on a walk through the park?”  Another step closer.

“Yes, Dean.”  An answering step.

“And will you let me kiss you when I drop you off at home?”  Two more steps.

“Yes,” and he swallowed hard.  A half step and now he was right in front of Dean, so close he was breathing him in.  “You could kiss me now, though.  If you wanted to.”

“You dare me to?” he challenged.

“Yes.”

Dean leaned down and pressed their lips together in a chaste kiss that still lit up Cas’ vision.  They moved their lips slowly, dragging out the feeling for a few more seconds before Dean pulled back to meet his eyes.  Liking what he saw, he cupped Cas’ cheek in his hand and stroked it with his thumb.  

The second kiss wasn’t nearly so tame.  

“Oh my god,” Jo whispered, effectively breaking the moment and forcing the two boys to jump away from each other.  “Finally, friggin _finally!”_

“Nice work, Sammy!” Charlie praised and high-fived him.  “I’ve been trying to get them together since Freshman year, and you do it with a sentence.  Well done, man, well done.”

Sam stood up and bowed dramatically, earning him a punch on the shoulder from Dean.  But given how Dean’s hand was now intertwined with Castiel’s, they were all pretty sure he’d forgive his younger brother.


End file.
